Enterprises may require individuals to plan and/or purchase goods and/or services. In one example, individuals may need to book travel. For example, travel arrangements are made on an individual basis, where individuals book flights, hotels, and other travel accommodations based on their own needs. As another example, a travel agent books travel arrangements for individuals. In such examples, an absence of contextual information can limit insight into appropriate travel accommodations for a particular individual and/or a particular trip. Further, it can be a relatively burdensome, manual effort to identify which hotel, which flight, which public transportation (if needed), and the like. In some instances, the travel arrangements are subsequently scrutinized for conformance to enterprise policies, and/or regulatory schema. Non-conforming travel arrangements can be resource-burdensome to audit.